The stereochemical course of anionic decarboxylation of α-sulfonyl carboxylic acids
✍ Scribed by E.J. Corey; Thomas H. Lowry
- Publisher
- Elsevier Science
- Year
- 1965
- Tongue
- French
- Weight
- 265 KB
- Volume
- 6
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Ol-Sulfony' carbanions of structure R-SO,-T (Rl)(R2) ACIDS Mass. 02138 can be generated from optically active precursors R-S02-C (Rl)(R2)(Y) in hydroxylic media and protonated to give optically active products, R-S02-CH(Rl)(R2), with high stereospecificity. This remarkable
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Intermediate dianions formed by nucleophilic attack of methyllithium on a-phenyl or a-phenylthio carboxylate salts fragment in highly coordinating solvents to produce stabilized carbanions. Once formed, these anions may be conveniently functionalized with various electrophilic reagents.
In investigations reported from several laboratories a-sulfonyl carbanions generated from optically active precursors have been shown to be capable of maintaining their asymmetry. 1,2,3 The studies on a-sulfonyl free radicals which we wish to describe here were undertaken with the intention of dete